Dear David Wygant“Should I ask her out?”

I still see this question in my emails regularly, even though it reminds me of being back at high school. It’s like when you’d write a note to that pretty girl in class you liked saying, “Will you be my girlfriend? Tick yes or no.”

But today’s Dear David is from a guy asking just that. The thing is he’s only 19 years old, and I want to set him on the right path. So many guys say they wish they’d met me when they were younger, so this is a great opportunity for this young man to benefit from my experience and the experience of the more mature guys and gals on the blog. Here’s his question…

“Dear David,

This probably sounds immature, but I’m 19 years old and not experienced with girls. I’m a quiet guy so I don’t always have much of a chance with girls.

Anyway, there’s this girl on my class I like a lot. One of the things I like so much about her is she’s so sweet and kind. Most the girls I meet here are quite rude and bitchy. It’s so nice to meet a girl who isn’t like the others.

She broke up with her boyfriend about a month ago and he was very different to me. He was the typical football QB, and I figure I don’t have much chance with her. We do talk though and she’s always smiling at me in a kind of shy way. I want to ask her out but in all honesty, I’m afraid she’ll reject me and I’ll feel an idiot. Is there any way to test her interest, before I ask her on a date?

Thanks David!

All the best


David Says…

Hey Raff,

You sound like a decent guy. But there are a couple of little tweaks you need to make to your current mindset. Just because her last boyfriend was a football player and possibly more confident than you, doesn’t mean you don’t stand a chance with her.

For all you know, after dating this guy she may have vowed she’d never date a football player again. She might want a nice quiet guy like you to date. You just don’t know, until….


And this is the second tweak you need to make to your mindset. You want to know whether she’d go on a date with you, but you’re worried in case she rejects you and you look stupid. Let’s say you take the easy option and don’t ask her out. You don’t have the risk of rejection anymore, but you also don’t have the possibility of her saying yes and all the fun you could have with her.

If she “rejects” you, why would you look silly?

If she’s as nice as you say she is, chances are she’ll just tell you nicely she wants to be friends and that’s it. No big deal, and no looking like an idiot. Life is all about putting yourself out there, and taking some chances. In fact, recently Jim Carrey was making a commencement speech, and in a one-minute segment, he sums it up perfectly.

I’ll let you see the video in a moment, but what he says is exactly right. In life, you may as well try to get the things you want. We get one chance at life, if you don’t spend your time doing the things you love or being with the people you enjoy, you’re going to get to the end of your life with regret.

I think you should just let this girl know you like her, and see if she’d be up for grabbing a coffee or something. Don’t go overboard. Just mention it during one of your conversations. Either she’ll say yes, or she’ll let you know she doesn’t see you that way. No harm done either way, and you could end up getting a date at the end of it!

Listen to this part of Jim Carrey’s speech, and you’ll hear what I’m talking about!